Methyl 8a-(hydroxymethyl)-5,6-dimethyl-5-[2-(3-oxo-2,6-dioxabicyclo[3.1.0]hexan-4-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

Details

• Internal ID: 20de9249-c4f7-4473-8b60-df8af60fe7fd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: methyl 8a-(hydroxymethyl)-5,6-dimethyl-5-[2-(3-oxo-2,6-dioxabicyclo[3.1.0]hexan-4-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC3C4C(O4)OC3=O)CCC=C2C(=O)OC)CO
• SMILES (Isomeric): CC1CCC2(C(C1(C)CCC3C4C(O4)OC3=O)CCC=C2C(=O)OC)CO
• InChI: InChI=1S/C21H30O6/c1-12-7-10-21(11-22)14(18(24)25-3)5-4-6-15(21)20(12,2)9-8-13-16-19(26-16)27-17(13)23/h5,12-13,15-16,19,22H,4,6-11H2,1-3H3
• InChI Key: PJEIFIYMLSWXAP-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₆
• Molecular Weight: 378.50 g/mol
• Exact Mass: 378.20423867 g/mol
• Topological Polar Surface Area (TPSA): 85.40 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9513	95.13%
Caco-2	+	0.5889	58.89%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8101	81.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8493	84.93%
OATP1B3 inhibitior	+	0.9250	92.50%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6168	61.68%
BSEP inhibitior	+	0.7110	71.10%
P-glycoprotein inhibitior	-	0.6083	60.83%
P-glycoprotein substrate	-	0.6387	63.87%
CYP3A4 substrate	+	0.6643	66.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8935	89.35%
CYP3A4 inhibition	-	0.6127	61.27%
CYP2C9 inhibition	-	0.7104	71.04%
CYP2C19 inhibition	-	0.8321	83.21%
CYP2D6 inhibition	-	0.9203	92.03%
CYP1A2 inhibition	-	0.7467	74.67%
CYP2C8 inhibition	+	0.4907	49.07%
CYP inhibitory promiscuity	-	0.8006	80.06%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5763	57.63%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9286	92.86%
Skin irritation	-	0.5826	58.26%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.6254	62.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4603	46.03%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.5200	52.00%
skin sensitisation	-	0.8798	87.98%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7099	70.99%
Acute Oral Toxicity (c)	I	0.6731	67.31%
Estrogen receptor binding	+	0.8530	85.30%
Androgen receptor binding	+	0.6479	64.79%
Thyroid receptor binding	+	0.6216	62.16%
Glucocorticoid receptor binding	+	0.7593	75.93%
Aromatase binding	+	0.6452	64.52%
PPAR gamma	+	0.5516	55.16%
Honey bee toxicity	-	0.8197	81.97%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9775	97.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.36%	83.82%
CHEMBL4072	P07858	Cathepsin B	97.96%	93.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.13%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.28%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.74%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.12%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.66%	97.25%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.79%	86.92%
CHEMBL230	P35354	Cyclooxygenase-2	86.26%	89.63%
CHEMBL2996	Q05655	Protein kinase C delta	85.74%	97.79%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.34%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.67%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.54%	97.14%
CHEMBL332	P03956	Matrix metalloproteinase-1	82.47%	94.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.46%	91.24%
CHEMBL2581	P07339	Cathepsin D	82.06%	98.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.59%	94.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.21%	95.83%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.11%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.96%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.91%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.11%	95.89%

Plants that contains it

• Nidorella ivifolia

Cross-Links

• PubChem: 162996794
• LOTUS: LTS0013667
• wikiData: Q105209915